DE69714974D1 - METHOD FOR SYNTHESISING POLYPYRROL AND POLYIMIDAZOLE CARBOXAMIDES ON SOLID CARRIERS - Google Patents
METHOD FOR SYNTHESISING POLYPYRROL AND POLYIMIDAZOLE CARBOXAMIDES ON SOLID CARRIERSInfo
- Publication number
- DE69714974D1 DE69714974D1 DE69714974T DE69714974T DE69714974D1 DE 69714974 D1 DE69714974 D1 DE 69714974D1 DE 69714974 T DE69714974 T DE 69714974T DE 69714974 T DE69714974 T DE 69714974T DE 69714974 D1 DE69714974 D1 DE 69714974D1
- Authority
- DE
- Germany
- Prior art keywords
- polyamides
- describes
- present
- carboxamides
- minor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6839—Triple helix formation or other higher order conformations in hybridisation assays
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/607,078 US6090947A (en) | 1996-02-26 | 1996-02-26 | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
PCT/US1997/003332 WO1997030975A2 (en) | 1996-02-26 | 1997-02-20 | Method for the synthesis of poly-pyrrole and poly-imidazole carboxamides on a solid support |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69714974D1 true DE69714974D1 (en) | 2002-10-02 |
DE69714974T2 DE69714974T2 (en) | 2003-05-08 |
Family
ID=24430722
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69714974T Expired - Lifetime DE69714974T2 (en) | 1996-02-26 | 1997-02-20 | METHOD FOR SYNTHESISING POLYPYRROL AND POLYIMIDAZOLE CARBOXAMIDES ON SOLID CARRIERS |
Country Status (8)
Country | Link |
---|---|
US (3) | US6090947A (en) |
EP (1) | EP0885189B9 (en) |
JP (1) | JP3231045B2 (en) |
AT (1) | ATE222890T1 (en) |
AU (1) | AU735022B2 (en) |
CA (1) | CA2247889C (en) |
DE (1) | DE69714974T2 (en) |
WO (1) | WO1997030975A2 (en) |
Families Citing this family (96)
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JP2002515897A (en) | 1996-02-26 | 2002-05-28 | カリフォルニア・インスティチュート・オブ・テクノロジー | Design, synthesis, and use of specific polyamide DNA-binding ligands |
EP1023288A1 (en) | 1996-02-26 | 2000-08-02 | California Institute Of Technology | Stereochemical control of the dna binding affinity, sequence specificity, and orientation-preference of chiral hairpin polyamides in the minor groove |
US6506906B1 (en) | 1996-02-26 | 2003-01-14 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
US6090947A (en) | 1996-02-26 | 2000-07-18 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
US6635417B1 (en) | 1996-07-31 | 2003-10-21 | California Institute Of Technology | Complex formation between DSDNA and oligomer of cyclic heterocycles |
US6555692B1 (en) | 1996-02-26 | 2003-04-29 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
CN1260006A (en) * | 1996-02-26 | 2000-07-12 | 加利福尼亚州技术学院 | Complex formation between dsDNA and oligomer of heterocycles |
US5998140A (en) | 1996-07-31 | 1999-12-07 | The Scripps Research Institute | Complex formation between dsDNA and oligomer of cyclic heterocycles |
CA2279574C (en) | 1997-01-31 | 2007-07-24 | The Horticulture & Food Research Institute Of New Zealand Ltd. | Optical apparatus |
CA2286232A1 (en) * | 1997-04-06 | 1998-11-05 | California Institute Of Technology | Dna-binding pyrrole and imidazole polyamide derivatives |
US6149867A (en) | 1997-12-31 | 2000-11-21 | Xy, Inc. | Sheath fluids and collection systems for sex-specific cytometer sorting of sperm |
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WO2000040605A2 (en) * | 1999-01-08 | 2000-07-13 | California Institute Of Technology | Compositions and methods relating to cyclic compounds that undergo nucleotide base pair-specific interactions with double-stranded nucleic acids |
US6673940B1 (en) * | 1999-01-08 | 2004-01-06 | California Institute Of Technology | Compositions and methods relating to cyclic compounds that undergo nucleotide base pair-specific interactions with double-stranded nucleic acids |
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US6559125B1 (en) | 2000-01-28 | 2003-05-06 | California Institute Of Technology | Polyamide-alkylator conjugates and related products and method |
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1996
- 1996-02-26 US US08/607,078 patent/US6090947A/en not_active Expired - Lifetime
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1997
- 1997-02-20 DE DE69714974T patent/DE69714974T2/en not_active Expired - Lifetime
- 1997-02-20 JP JP53042597A patent/JP3231045B2/en not_active Expired - Lifetime
- 1997-02-20 EP EP97916720A patent/EP0885189B9/en not_active Expired - Lifetime
- 1997-02-20 AU AU25268/97A patent/AU735022B2/en not_active Ceased
- 1997-02-20 WO PCT/US1997/003332 patent/WO1997030975A2/en active IP Right Grant
- 1997-02-20 AT AT97916720T patent/ATE222890T1/en not_active IP Right Cessation
- 1997-02-20 CA CA002247889A patent/CA2247889C/en not_active Expired - Fee Related
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1999
- 1999-07-22 US US09/360,344 patent/US6683189B1/en not_active Expired - Lifetime
- 1999-07-22 US US09/359,921 patent/US6545162B1/en not_active Expired - Lifetime
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AU735022B2 (en) | 2001-06-28 |
US6090947A (en) | 2000-07-18 |
CA2247889A1 (en) | 1997-08-28 |
ATE222890T1 (en) | 2002-09-15 |
DE69714974T2 (en) | 2003-05-08 |
JP3231045B2 (en) | 2001-11-19 |
EP0885189A2 (en) | 1998-12-23 |
JP2000503324A (en) | 2000-03-21 |
US6545162B1 (en) | 2003-04-08 |
EP0885189B1 (en) | 2002-08-28 |
CA2247889C (en) | 2006-02-14 |
AU2526897A (en) | 1997-09-10 |
WO1997030975A2 (en) | 1997-08-28 |
EP0885189B9 (en) | 2003-04-02 |
US6683189B1 (en) | 2004-01-27 |
WO1997030975A3 (en) | 1997-10-16 |
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